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NMR analysis of (1S, 1aR, 6aR)-2’, 3’, 6, 6a-tetrahydrospiro cycloprop a indene-1(1aH), 1’- 1H indene

NMR analiza (1S,1aR,6aR)-2’,3’,6,6a-tetrahidro-spiro[cikloprop[a]inden-1(1ah),1’-[ 1h]indena]

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2005
0352-51390510133S.pdf (95.59Kb)
Authors
Spiteller, Peter
Jovanović, Jovan
Spiteller, Michael
Article (Published version)
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Abstract
The aldol condensation product of 1H-indan-1-one, (2E)-2-(2,3-dihydro-1H-in den-1-ylidene)-2,3-dihydro-1H-inden-1-one, subjected to Huang–Minlon reduction conditions was shown, via 1D and 2D NMR analysis, to be a mixture of (1S,1aR,6aR)-2’,3’,6,6a-tetrahydro-spiro cycloprop a indene-1(1aH),1’ 1H indene and its 1R,1aS,6aS enantiomer and not 2,3,1’,3’-tetrahydro- 1,2’ -biindenylidene as originally expected. The full NMR assignment, the coupling constants in the proton NMR, and the couplings in the HMBC and NOESY of the title compound are summarized in the Table.
Pokazano je pomoću 1D i 2D NMR analize da (2E)-2-(2,3-dihidro-1H-inden-1-iliden)-2, 3-dihidro-1H-inden-1-on, dobiven aldolnom kondenzacijom 1H-indan-1-ona, podvrgnut Huang–Minlonovoj redukciji daje smešu (1S,1aR,6aR)-2’,3’,6 6a-tetrahidro-spiro[cikloprop[a]inden-1(1aH),1’-[1H]indena] i njegovog 1R,1aS,6aS enantiomera, a ne 2,3,1’,3’-tetrahidro-[1,2’]-biindeniliden kako se prvobitno očekivalo. Potpuni NMR raspored, konstante kuplovanja protona i HMBC i NOESY kuplovanje jedinjenja u naslovu dati su zbirno u tabeli.
Keywords:
dimer of indene / NMR assignment / JHH / HMBC / NOESY
Source:
Journal of the Serbian Chemical Society, 2005, 70, 10, 1133-1136
Publisher:
  • Serbian Chemical Society, Belgrade

ISSN: 0352-5139

WoS: 000233676900001

Scopus: 2-s2.0-31544434284
[ Google Scholar ]
1
1
Handle
https://hdl.handle.net/21.15107/rcub_technorep_795
URI
http://TechnoRep.tmf.bg.ac.rs/handle/123456789/795
Collections
  • Radovi istraživača / Researchers’ publications (TMF)
Institution/Community
Tehnološko-metalurški fakultet
TY  - JOUR
AU  - Spiteller, Peter
AU  - Jovanović, Jovan
AU  - Spiteller, Michael
PY  - 2005
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/795
AB  - The aldol condensation product of 1H-indan-1-one, (2E)-2-(2,3-dihydro-1H-in den-1-ylidene)-2,3-dihydro-1H-inden-1-one, subjected to Huang–Minlon reduction conditions was shown, via 1D and 2D NMR analysis, to be a mixture of (1S,1aR,6aR)-2’,3’,6,6a-tetrahydro-spiro cycloprop a indene-1(1aH),1’ 1H indene and its 1R,1aS,6aS enantiomer and not 2,3,1’,3’-tetrahydro- 1,2’ -biindenylidene as originally expected. The full NMR assignment, the coupling constants in the proton NMR, and the couplings in the HMBC and NOESY of the title compound are summarized in the Table.
AB  - Pokazano je pomoću 1D i 2D NMR analize da (2E)-2-(2,3-dihidro-1H-inden-1-iliden)-2, 3-dihidro-1H-inden-1-on, dobiven aldolnom kondenzacijom 1H-indan-1-ona, podvrgnut Huang–Minlonovoj redukciji daje smešu (1S,1aR,6aR)-2’,3’,6 6a-tetrahidro-spiro[cikloprop[a]inden-1(1aH),1’-[1H]indena] i njegovog 1R,1aS,6aS enantiomera, a ne 2,3,1’,3’-tetrahidro-[1,2’]-biindeniliden kako se prvobitno očekivalo. Potpuni NMR raspored, konstante kuplovanja protona i HMBC i NOESY kuplovanje jedinjenja u naslovu dati su zbirno u tabeli.
PB  - Serbian Chemical Society, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - NMR analysis of (1S, 1aR, 6aR)-2’, 3’, 6, 6a-tetrahydrospiro cycloprop a indene-1(1aH), 1’- 1H indene
T1  - NMR analiza (1S,1aR,6aR)-2’,3’,6,6a-tetrahidro-spiro[cikloprop[a]inden-1(1ah),1’-[ 1h]indena]
EP  - 1136
IS  - 10
SP  - 1133
VL  - 70
UR  - https://hdl.handle.net/21.15107/rcub_technorep_795
ER  - 
@article{
author = "Spiteller, Peter and Jovanović, Jovan and Spiteller, Michael",
year = "2005",
abstract = "The aldol condensation product of 1H-indan-1-one, (2E)-2-(2,3-dihydro-1H-in den-1-ylidene)-2,3-dihydro-1H-inden-1-one, subjected to Huang–Minlon reduction conditions was shown, via 1D and 2D NMR analysis, to be a mixture of (1S,1aR,6aR)-2’,3’,6,6a-tetrahydro-spiro cycloprop a indene-1(1aH),1’ 1H indene and its 1R,1aS,6aS enantiomer and not 2,3,1’,3’-tetrahydro- 1,2’ -biindenylidene as originally expected. The full NMR assignment, the coupling constants in the proton NMR, and the couplings in the HMBC and NOESY of the title compound are summarized in the Table., Pokazano je pomoću 1D i 2D NMR analize da (2E)-2-(2,3-dihidro-1H-inden-1-iliden)-2, 3-dihidro-1H-inden-1-on, dobiven aldolnom kondenzacijom 1H-indan-1-ona, podvrgnut Huang–Minlonovoj redukciji daje smešu (1S,1aR,6aR)-2’,3’,6 6a-tetrahidro-spiro[cikloprop[a]inden-1(1aH),1’-[1H]indena] i njegovog 1R,1aS,6aS enantiomera, a ne 2,3,1’,3’-tetrahidro-[1,2’]-biindeniliden kako se prvobitno očekivalo. Potpuni NMR raspored, konstante kuplovanja protona i HMBC i NOESY kuplovanje jedinjenja u naslovu dati su zbirno u tabeli.",
publisher = "Serbian Chemical Society, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "NMR analysis of (1S, 1aR, 6aR)-2’, 3’, 6, 6a-tetrahydrospiro cycloprop a indene-1(1aH), 1’- 1H indene, NMR analiza (1S,1aR,6aR)-2’,3’,6,6a-tetrahidro-spiro[cikloprop[a]inden-1(1ah),1’-[ 1h]indena]",
pages = "1136-1133",
number = "10",
volume = "70",
url = "https://hdl.handle.net/21.15107/rcub_technorep_795"
}
Spiteller, P., Jovanović, J.,& Spiteller, M.. (2005). NMR analysis of (1S, 1aR, 6aR)-2’, 3’, 6, 6a-tetrahydrospiro cycloprop a indene-1(1aH), 1’- 1H indene. in Journal of the Serbian Chemical Society
Serbian Chemical Society, Belgrade., 70(10), 1133-1136.
https://hdl.handle.net/21.15107/rcub_technorep_795
Spiteller P, Jovanović J, Spiteller M. NMR analysis of (1S, 1aR, 6aR)-2’, 3’, 6, 6a-tetrahydrospiro cycloprop a indene-1(1aH), 1’- 1H indene. in Journal of the Serbian Chemical Society. 2005;70(10):1133-1136.
https://hdl.handle.net/21.15107/rcub_technorep_795 .
Spiteller, Peter, Jovanović, Jovan, Spiteller, Michael, "NMR analysis of (1S, 1aR, 6aR)-2’, 3’, 6, 6a-tetrahydrospiro cycloprop a indene-1(1aH), 1’- 1H indene" in Journal of the Serbian Chemical Society, 70, no. 10 (2005):1133-1136,
https://hdl.handle.net/21.15107/rcub_technorep_795 .

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